2-Hydroxy-4-(methylthio)butyric acid

HMB Strukturformel.svg 2-Hydroxy-4-(methylsulfanyl)butanoic acid 2-Hydroxy-4-(methylthio)-butanoic acid α-Hydroxy-γ-(methylthio)-butyric acid Desmeninol Alimet 583-91-5 correct CAS 2104213 137228 10946 DB15832 209-523-0 11427 Z94465H1Y7 CSCCC(O)C(O)=O 1S/C5H10O3S/c1-9-3-2-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8) ONFOSYPQQXJWGS-UHFFFAOYSA-N 5 10 3 1 colorless or white solid 2-Hydroxy-4-(methylthio)butyric acid https://pubchem.ncbi.nlm.nih.gov/compound/11427#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov 28 April 2022 en 05 07 Danger 315 318 412 264 264+265 273 280 302+352 305+354+338 317 321 332+317 362+364 501 2-Hydroxy-4-(methylthio)butyric acid is an organic compound with the structural formula CH3SCH2CH2CH(OH)CO2H. It is a white solid. In terms of functional groups, the molecule is a α-hydroxy carboxylic acid and a thioether. The compound is structurally related to the amino acid methionine by replacement of the amine with a hydroxy group. The compound is produced commercially in racemic form from acrolein by conjugate addition of methanethiol followed by formation and hydrolysis of a cyanohydrin.10.1021/jf048827q Hydrolysis of Nitriles Using an Immobilized Nitrilase: Applications to the Synthesis of Methionine Hydroxy Analogue Derivatives 2004 Rey Patrick Rossi Jean-Christophe Taillades Jacques Gros Georges Nore Olivier Journal of Agricultural and Food Chemistry 52 26 8155–8162 15612811 it is used as a substitute for methionine in animal feed.10.1093/ps/81.6.838 Relative Effectiveness of Methionine Hydroxy Analog Compared to DL-Methionine in Broiler Chickens 2002 Lemme A. Hoehler D. Brennan JJ Mannion PF Poultry Science 81 6 838–845 12079051 free In nature, the compound is also an intermediate in the biosynthesis of 3-dimethylsulfoniopropionate, precursor to natural dimethyl sulfide.10.1038/nmicrobiol.2017.9 Dimethylsulfoniopropionate Biosynthesis in Marine Bacteria and Identification of the Key Gene in this Process 2017 Curson Andrew R. J. Liu Ji Bermejo Martínez Ana Green Robert T. Chan Yohan Carrión Ornella Williams Beth T. Zhang Sheng-Hui Yang Gui-Peng Bulman Page Philip C. Zhang Xiao-Hua Todd Jonathan D. Nature Microbiology 2 5 17009 28191900 21460292 https://ueaeprints.uea.ac.uk/id/eprint/62649/1/Todd_Figure_1.pdf References Category:Alpha hydroxycarboxylic acids Category:Methylthio compounds